Long Term Plan
by FabricioEvil
Summary: After many failed attempts, Jessie of Team Rocket finally decides there is only one nefarious way for her to catch the twerp's Pikachu once and for all. (Oneshot Ash/Jessie, LEMON warning)


Author's Note: This is a lemon scene set in an alternate universe version of the first season of the Pokémon anime. You've read the characters involved, you've seen the rating. If neither are for you then you know what to do.

Disclaimer: Pokémon is property of Nintendo and Game Freak. I do not own anything.

Jessie of Team Rocket waited for James to finish observing their three targets when she thought to herself, "I can't believe I can get frustrated like this." For Jessie, the attempts by her partner and Meowth had racked up to two dozen times in their attempts to capture just one Pikachu. All of the mounting failures were getting to her and she found herself wanting some level of stress relief. "Who should I look to though? James isn't good enough... Meowth... Why the hell did I even just consider that?" She looked down at her full-figured body when she smirked to herself, "Whatever. It shouldn't be so hard to get someone with a body like mine." She had an idea pop in her head when she decided, "Then again I know who I could probably go for... It might even be enough to kill two birds with one stone." She didn't bother bringing up any commands to James while she waited for him to finish his observation. Tonight was going to present the opportunity she needed...

* * *

Night had fallen in the forest and a trainer wandered through the woods. "Yeah, just another day where I beat Team Rocket. I wonder if they ever will get tired of trying to get Pikachu?" Ash wondered to himself. He had just recently left Celadon City where he earned the Rainbow Badge. It was a fairly exciting day when that happened especially after trying to save several Pokémon from a burning gym. At the moment he was only in the mood to walk off what energy remained in his system after the days travel. He was about to arrive in HopHopHop Town in a few days to mark the first step in which him and his friends would find the Fuchsia Gym.

Ash was about to continue his walk before he found himself pushed aside from his path. Ash tried to figure out who just pushed him and saw his attacker once she stopped moving. The red bombshell known as Jessie of Team Rocket had grabbed hold of his hands when he asked, "What the?! Jessie?!"

Jessie pushed Ash's wrists above him against the nearest tree when she commanded, "Here's the deal twerp and it's going to be pretty mutual. You're going to follow every command I give you and you're going to give me the best ravishing I ever had."

Ash looked away from her gaze when he answered, "Uh... I don't... I don't think..."

Jessie pressed her breasts against his chest when she told him, "I think you do know what I mean. You've got the hormones acting up don't you? Just act on them." Unfortunately for Ash she was right. He could feel his blood rushing as soon as Jessie's fleshy orbs pressed against him. It made matters worse that she not only wanted him but she was demanding it of all things.

"Brock would kill to be in this position. I... I guess she was always... kind of pretty..." He steered himself clear of that train of thought when he realized just what exactly he was thinking at the time. "What?!" Other than realizing that Brock never showed any interest in Jessie in that way before he realized just what Jessie was asking for. He instantly hoped to find his friends somewhere nearby as he moved his head from left to right out of desperation. Nowhere to be seen he protested his captor's command, "No way! I'm not doing that with you Jessie!"

"Oh are you now?" Ash just realized that Jessie's latex glove worked its way into his pants when she commented, "This little man doesn't seem to agree with you..." Even worse Ash found out about the grown erection in his pants from his close encounter when Jessie pointed it out.

"But... That's..." Before Ash could explain he saw Jessie pull down his jeans in a single motion letting his manhood free into the air. "AH!" He rushed for an answer when he told her, "You're the one who's making me do that!"

Jessie looked up at the young boy grinning, "Oh so you admit it huh?" Ash was lost for an answer when Jessie moved her face level to his throbbing organ, "Just sit tight twerp. We want this to be pleasurable for both of us don't we?" Before he could protest he saw Jessie move in for the taking when her mouth took in his length. He face made its way to the base before Ash could even try to protest. He let out a gasp when he felt Jessie's saliva surround his member and was exposed to the cool air again. Ash tried to let out another protest but felt Jessie's head move to his tip before she moved her mouth all the way down his length. Right after that motion Jessie's oral administration became a motion with Ash attempting to even let out a sound.

A minute had passed before Ash stuttered, "Ah! Ah... J-Jess... Jessie... AH!" He stopped himself when he felt a small nip on his member from Jessie's teeth. As if to remind him he looked down to see Jessie giving a warning glare. Ash gulped before nodding and continued to take the movements of Jessie's mouth. Before long Ash didn't make any attempt to protest and ended up too lost in the constant exposure to the cool air when his manhood was exposed to the air.

Ash felt a pressure building in him that made its way down to his loins. As if Jessie seemed to know that this moment of truth was coming she began to move her mouth back and forth at a quicker rate. This moment left Ash to moan in pleasure from the constant attack and before long yelled from the explosion erupting from the tip of his penis. Jessie removed herself from the squirting organ with some of Ash's ejaculation in her mouth but only to feel it land onto her face and in her hair. Jessie grinned wickedly as she licked some of Ash's cum asking, "There now. That wasn't so bad now was it twerp?" Ash didn't respond as he kept panting from the orgasm. He leaned against the tree hoping to rest but Jessie pushed him down to the ground on his back commanding, "Don't even think we're near finished twerp. It's time for you to return the favor."

Ash looked up and asked, "How am I supposed to -" Before he could finish Jessie lifted up her white uniform skirt to expose her bare vagina and planted her knees in between his face.

She sat down on Ash's face before commanding, "Now start twerp." When she didn't feel his tongue come out she added, "Start licking me or I'll squeeze your throat!" At that threat she felt a slippery presence worm its way into her nether regions. "Ah..." Jessie moaned as she savored the younger boy's tongue slip through her. It only took a few seconds before she could feel Ash's tongue slither and pop in and out of her feminine area. Jessie eagerly accepted this when she asked, "Ah... Now there we go... Not so bad now is it twerp?" Ash's eyes were shut as he tried to grit his way through the act. Jessie in the meantime continued to enjoy her captive's slippery tongue in her while continuing to moan at the feeling. It only took a few more seconds before Jessie began to buck her hips against Ash's face treating his tongue as if it were the cock she wanted in her.

It took another few minutes before Jessie began to feel her orgasm rapidly approaching while Ash continued to lick her. She bucked her hips a few more times before commanding, "Now just take it twerp! Keep taking it and you get to see what it's like!" She thrust herself down a few more times before she moaned out her orgasm and let her juices flow over Ash's face. Jessie savored the release from her body for a few seconds before she lifted herself from the boy beneath her.

Ash gasped for air and accidentally took in some of the ejaculation into his mouth. He gagged once before asking, "That's got to be what you were hoping for wasn't it Jessie?"

Jessie didn't seem to agree when she moved herself further down Ash's body answering, "We can't just leave it here now can we? You are the one with the erection after all." Jessie positioned her wet vagina over Ash's new erection when she prepared, "Now I think I'm all ready for the real thing..."

Ash was taken aback when she said this asking, "Jessie... Are you actually going to -"

Jessie gave one final wicked smile before she answered, "Oh yes I am." In one swift motion Jessie squat down to impale herself on Ash's throbbing erection and took his entire length in one dive. "Ah! Ah yes... Oh it's nice to have a dick in me again!" Jessie proclaimed when she adjusted to Ash's presence inside her.

Ash was in the meantime adjusting to the sudden tightness surrounding his manhood and felt a rush of shame through him. Not only was his first sexual experience with someone he should despise, but he was enjoying it. "J... Jessie... This is..."

"Shut up and let me take this twerp! I'm not going to deny myself what I'm after!" Jessie didn't take any more time in preparing to milk her prized catch for all it was worth. She began to bounce herself up and down from Ash's eager cock seeking to erode its hardness. Jessie moaned to her movements as she rose to remove herself from Ash's hardness only to have it enter her again. It wasn't long before she began to hear Ash beneath her giving the same type of moans. Jessie's mission was going well above the intended plan.

Before long she felt Ash's hips moving up as well. Jessie pressed her hips down to his when she asked, "And I think you're starting to like it too huh twerp? Just try to keep up with me." At that challenge Jessie picked up the speed of her bounces to collide with Ash's hips. The two truly enjoying the rush of passion they were in.

"J... Jessie... It's so... It's so good..." Ash said as he continued to pump into Jessie's canal. The experience began to drive him insane as he let his hormones and instincts take control of him. He had now completely surrendered to Jessie's desires. It was the most enjoyable loss Ash had ever endured.

Jessie did everything she could to pin Ash to the ground when she commanded, "Ah yes... Oh yes yes... That's what I'm talking about... Ooh just lie there you little twerp..." The two continued their union for what seemed like forever while they were both lucky no one had stopped by to notice them.

As Ash continued to pump into Jessie he felt the same pressure from Jessie's oral attack earlier build in his loins when he warned, "Oh... shit... Jessie... I don't think..."

"Do it twerp! Do it now!" Jessie began to pick up the pace of her squats as she moved at a speed faster than before. Ash could feel her canal squeezing even tighter than he thought possible and was subject to Jessie's final command, "Just cum already damn it! Just cum!" Ash didn't protest as he continued to push into her and felt Jessie's juices begin to flow again. Eventually it became too much for him to handle and he gave the final thrust. The explosion within Jessie brought Ash's semen into her womb and they both yelled out of unadulterated primal enthusiasm. A few seconds had past after their orgasm when Jessie fell down on top of Ash. Her full breasts pressed against him again while she did everything to keep his dick within her. Minutes of rest passed before Jessie picked herself up from Ash's body commenting, "Mmmm... Now that was delightful."

Ash was still awake and shocked at their recent act when he answered, "I guess... I guess it was..."

Jessie took the comment as a challenge when she asked, "Oh you only guess huh? Maybe you need more convincing?" Ash was about to ask something but Jessie pressed a finger to his mouth when she told him, "Don't bother asking any questions. You should know by now that I have all the answers on this subject." Jessie lifted her vice from Ash and began to crawl down to his currently exhausted cock. Ash thought he was about to receive her mouth again but found that Jessie was still full of surprises. She lifted the top of her shirt to expose her full breasts to Ash and prepared for the next round of stimulation.

Jessie sandwiched Ash's manhood with her breasts and moved them up and down to encourage its growth. By now with his member mixed with her saliva and sexual juices, it only took a few seconds before Ash found himself getting excited again.

Jessie eyed the growing length when she commented, "Hm hm hm... Looks like you're excited already about going at it again."

Several seconds had passed before Ash finally let out his wish as a command, "Damn it Jessie! Just let me do it already!"

Jessie showed a face of feigned surprise when she asked, "Oh taking command are you?" Jessie lay back on her fours presenting her womanhood to Ash offering, "Well why don't you come over and show me what you can do Mr. man."

Ash didn't need to be told twice. He threw off his shirts and pressed his chest to Jessie's breasts while this time being the one to take his captor. Ash was as quick to take Jessie this time as she was when he shoved himself in. "Ah! Oh fuck!" Right after those words Ash was pushing and pulling his third erection into Jessie and ravishing her for all she was worth. Jessie found this position much more exciting leaving her to command, "Oh yes! Oh yes twerp! Now that's the sort of thing I want!"

Ash smirked from the act when he warned, "I hope you do!" He pushed Jessie to the ground forcing her arms and legs to sprawl from his push. His hands took hold of her hips while he continued to plunge and moan out of sheer pleasure.

Still hoping to get more out of him Jessie commanded, "Take me harder! Do it faster!"

Ash groaned before protesting, "Stop telling me what to do!"

Jessie let out a small laugh when she threw back, "Like you'd even protest!" Instead of answering, Ash began to push in and pull out of Jessie faster than before. Now he wanted to own this woman and he was going to do everything to prove his dominance. Jessie laugh was mixed with moans when she continued to take in the younger boy's eager manhood while she held onto his shoulders to ensure that he wouldn't pull out. Her breasts slapped up and down in front of Ash as he brought his lower body to collide with hers.

Ash couldn't let go of the opportunity anymore when he brought an arm around Jessie's torso and brought it up to his. Her breasts smashed against his chest while Ash groaned and pushed himself into Jessie with every bit of stamina he had remaining. Both parties were at a loss for words when they were caught up in this moment only reduced to moans of primal lust to be satiated.

Ash was still thrusting himself into Jessie when he began to feel another orgasm coming. He made an effort to warn Jessie, "Ah shit... Damn... Jessie I'm getting there again!"

Jessie began to feel her vagina tightening around him and demanded, "Do it twerp! Let loose in me!" The two let out their final passionate moans before their mutual orgasm hit leaving the two of them to revel in the final release for that night. The two fell down to the grass together side by side left to rest from their lovemaking.

Once the afterglow had passed for a while Jessie looked next to her catch as she giggled, "So... Looks like you managed to enjoy this as much as I did."

Ash was slightly out of breath when he answered, "I... You're right. That was pretty nice Jessie."

Jessie turned his face to her when she told him, "Just keep this our little secret for now. One day I'll be sure that your really get to enjoy everything I have to offer."

"I think I can live with that." Not another word was said as Jessie French kissed Ash and both passed out for the night.

* * *

Months had passed as Ash's affair with Jessie continued. After losing in the League he needed the help of his friends Brock and Misty to help bring back his passion for becoming a better trainer. The three had stopped in a Pokémon Center on the way to Pallet Town where Brock was flirting with Nurse Joy. This left Ash, Pikachu, and Misty together where they could find out what to do next on their journey together.

As Ash continued his conversation with Misty he decided that now was time to spill everything. Unfortunately he didn't find it to be an easy topic to start when he told her, "Uh Misty I'm going to have to tell you something."

"Okay, what's wrong?"

"Oh nothing. Just that the little twerp here knows who he wants to be with forever." Jessie said coming out of nowhere. Now visible with a baby bump and her arm near Ash's chair it became immediately clear who the father was.

"WHAT?!" Misty pointed to the pregnant woman in question, "Ash are you serious Ash?! With Jessie?!"

"Pi-Pika?!" Pikachu asked in the same shocked tone.

Ash stumbled for an answer, "I... I know it's weird but it all happened so..."

"Don't even bother trying to talk your way out of this Ash! If you really enjoy having her so much then I hope you two stay happily ever after! Goodbye!" Misty turned away and stomped off.

"Wait Misty!"

Before Ash could run after her Jessie placed a hand on Ash's shoulder when she giggled commenting, "How do you like that Ash? Looks like we're hooked together for life now."

Ash felt guilt hang over him like a brick when he reluctantly agreed, "Uh... Yeah. Guess we are."

Jessie pointed to his final companion when she added, "And as such we have to share everything... Including that Pikachu of yours."

"What now?!"

"Pika?! Cha?!"


End file.
